Some word cloud fun with Wordle!

When we published 100 Startup Reads We Love, Matt discovered a tool called Wordle which generates simple, attractive word clouds. I spent an hour creating clouds from personally-relevant chunks of text, here they are!

*I manually removed common/boring words on top of what Wordle automatically does…eg, “startups” for 100 reads

From the RSS feed for this blog:


From my first draft of the ebook How To Live Forever:


From 100 Startup Reads (using titles, author names, and our short descriptions):


Try Wordle sometime! It’s free and (can be) insightful :)

Amazing Media – 10 recommended readings

Recently I’ve begun saving and annotating my favorite blog posts, articles, videos, etc. Here’s the page where I’ll add new stuff (and old stuff, re-discovered).

I’ve learned that the value of great media is not the first time you consume it, but re-absorbing and re-experiencing it over time (and doing so mindfully).

98% of what we consume is crap – shouldn’t we treasure the 2%? You don’t see tennis players practice a new forehand once and just walk away. And there’s a reason why organized religions have ONE TEXT that they read, re-read, and re-re-read.

Here are 10 of my favorites:

Disappointed bear (c/o Buzzfeed)
Disappointed bear (c/o Buzzfeed)
  1. It’s Not About You: The Truth About Social Media Marketing by Tim O’Reilly (LinkedIn) – the most effective social media marketing is creating tools and content to help communities achieve their goals. Snippet: Your job, in short, is to uncover and activate latent social networks and interest groups by helping them to reach their own goals.
  2. The Dividing Line (Max Cho) – simple yet profound. If anyone is curious what Jeff Bezos is thinking…
  3. 10 Charts About Sex (OkCupid blog) – people are fascinating. Sex is fascinating. People’s sex habits, man! Snippet: Curvy women pass skinny ones in self-confidence at age 29 and never look back. They also consistently have the highest sex drive among the groups. Curvy, as a word, has the strongest sensual overtones of all our self-descriptions. So we’re getting a little insight into the real-world implications of a label.
  4. Applied Philosophy, a.k.a. “Hacking” by Paul Buchheit (Blogspot) – great and simple explanation of a valuable outlook on life and work. Although as important is WHAT you work on – problem choice is as important as the HOW. Snippet: Sometimes we catch a glimpse of the truth, and discover the actual rules of a system. Once the actual rules are known, it may be possible to perform “miracles” — things which violate the perceived rules.
  5. The Puzzle by Christopher Michel ( – beautiful and profound piece by Chris Michel on travel and by extension, life. Snippet: But the answers can’t be found in accumulating more. You knew that already. Well, so did I, but I’m not sure I really believed it. I do now. Happiness is reality minus expectations. And Americans, in particular, have some pretty high expectations. You do the math.
  6. That Which Does Not Kill Me Makes Me Stranger ( – fascinating reporting on Jure Robic, one of the world’s greatest ultra-endurance athletes. Snippet: The craziness is methodical, however, and Robic and his crew know its pattern by heart. Around Day 2 of a typical weeklong race, his speech goes staccato. By Day 3, he is belligerent and sometimes paranoid. His short-term memory vanishes, and he weeps uncontrollably. The last days are marked by hallucinations: bears, wolves and aliens prowl the roadside; asphalt cracks rearrange themselves into coded messages. Occasionally, Robic leaps from his bike to square off with shadowy figures that turn out to be mailboxes. In a 2004 race, he turned to see himself pursued by a howling band of black-bearded men on horseback.
  7. 33 Animals Who Are Extremely Disappointed In You (Buzzfeed) – hilarious photos
  8. What Is Your Biggest Secret Desire That You Are Ashamed Of Telling Anyone? Reddit – love reddit for precisely these sorts of half-crazy, half-brutally honest windows into human psychology. The top vote-getter: In the middle of the night, I would pack one bag and drive away from my life. Not look back for one second and drive clear across the country. Find a small, rural town and just rebuild where nobody has an idea of who I am.
  9. Cities and Ambition by Paul Graham ( – a personal favorite among PG’s non-startup essays. Snippet: How much does it matter what message a city sends? Empirically, the answer seems to be: a lot. […] Most people who did great things were clumped together in a few places where that sort of thing was done at the time.
  10. George Orwell: Why I Write ( – Snippet: And looking back through my work, I see that it is invariably where I lacked a political purpose that I wrote lifeless books and was betrayed into purple passages, sentences without meaning, decorative adjectives and humbug generally.

When You Are Old by William Butler Yeats

My all-time favorite poem. I read it for the first time as a college freshman. It just stuck.

There are many reasons why I like it – the rhyme and rhythm, the beautiful phrasing, the tender depiction of true love. But – like all great works of art – it leaves you with more questions than answers, wanting more.

Is Yeats talking about unrequited love? Or is he reminding us of the undefeatable passage of time, the temporality of all things? Or is he reminiscing on a deep relationship that has faded like the embers of a dying fire? Crazy stuff.

Here it is:

by: William Butler Yeats (1865-1939)

WHEN you are old and grey and full of sleep,
and nodding by the fire, take down this book,
And slowly read, and dream of the soft look
Your eyes had once, and of their shadows deep;

How many loved your moments of glad grace,
And loved your beauty with love false or true,
But one man loved the pilgrim soul in you,
And loved the sorrows of your changing face;

And bending down beside the glowing bars,
Murmur, a little sadly, how Love fled
And paced upon the mountains overhead
And hid his face amid a crowd of stars.

The Good Life: Lessons from Ben Franklin’s 13 Virtues

Ben's booklet w/ 13 Virtues
Ben’s booklet w/ 13 Virtues

Too lazy, don’t want to read: download my 2-page PDF guide to Ben Franklin’s 13 Virtues.

This is my second Good Life guide. Read the first one here (on Rick Warren’s Purpose-Driven Life). If you’re curious why I’m doing this, the first one will help.

From these books, I’ll share insights, conclusions, and questions from history’s greatest thinkers and doers on finding purpose, meaning, and fulfillment. My goal is to provide some answers, and probably more questions, to living what Aristotle calls “eudemonia”, or simply, “the good life”.

It’s a 2-page PDF, free to download and share. Here’s the link to view it as a read-only Google Doc.

I’ve embedded a section below. As this is my second Good Life guide, I humbly ask for any and all feedback, advice, thoughts. I plan to write a LOT of these – I need your help to make them the best resources they can be.

Thanks and enjoy!


Franklin always carried a booklet with these 13 virtues. Each time he disobeyed a virtue, he’d mark it in his booklet. Since he focused on one virtue per week, he’d complete 4 cycles each year (13 virtues, 52 weeks). Here’s my (loose) interpretation of his virtues:

1. Temperance. Don’t overeat or overdrink
2. Silence. Speak only when you have something good to say
3. Order. Organize your life; pay attention to ALL aspects of your work
4. Resolution. Always do what you say you’ll do
5. Frugality. Spend little and spend wisely
6. Industry. Use your time wisely; stop doing wasteful things
7. Sincerity. Don’t lie; be honest and fair
8. Justice. Don’t harm others or ignore your obligations to them
9. Moderation. Avoid extremes; don’t hold grudges
10. Cleanliness. Regularly clean your body, your clothes, and your home
11. Tranquillity. Don’t get upset at small or unavoidable things
12. Chastity. Only have sex for health or babies, and never hurt others
13. Humility. Be super humble

Here’s a version with Ben’s original wording.

That’s it. Click here to download the full 2-page PDF!

Here’s a list of all 1-page cheatsheets, and a list of all books.

9 Highlights from Peter Thiel’s Startup Class Notes

I spent 4 hours reading through Blake Master’s notes from Peter Thiel’s startup class.

First, HUGE thanks to Blake for writing such detailed and thoughtful notes. After reading them, I *almost* felt like I was in the class, and I learned a TON in a short period of time.

In the spirit of being more mindful about what I consume & learn, here are some of my biggest takeaways:

1. True innovation is going from 0 to 1, not 1 to n. Google’s search technology was a 0 to 1 problem. They had to create something completely new, with relatively few precedents or comparables. The numerous Groupon clones are solving 1 to n problems, since the core product innovation has been accomplished.

Maybe we focus so much on going from 1 to n because that’s easier to do. There’s little doubt that going from 0 to 1 is qualitatively different, and almost always harder, than copying something n times. And even trying to achieve vertical, 0 to 1 progress presents the challenge of exceptionalism; any founder or inventor doing something new must wonder: am I sane? Or am I crazy?

Anyone on a mission tends to want to go from 0 to 1. You can only do that if you’re surrounded by others to want to go from 0 to 1.

2. Great companies create meaningful value that lasts, and they (ideally) capture a lot of that value.

Great companies do three things. First, they create value. Second, they are lasting or permanent in a meaningful way. Finally, they capture at least some of the value they create.

Consider great tech companies. Most have one decisive advantage—such as economies of scale or uniquely low production costs—that make them at least monopoly-esque in some important way. A drug company, for instance, might secure patent protection for a certain drug, thus enabling it to charge more than its costs of production. The really valuable businesses are monopoly businesses. They are the last movers who create value that can be sustained over time instead of being eroded away by competitive forces.

3. Start with a small, or new, market; dominate it; then expand to adjacent markets and grow larger over time

First, you want to find, create, or discover a new market. Second, you monopolize that market. Then you figure out how to expand that monopoly over time.

Markets that are too big are bad for all the reasons discussed above; it’s hard to get a handle on them and they are usually too competitive to make money.

The best kind of business is thus one where you can tell a compelling story about the future. The stories will all be different, but they take the same form: find a small target market, become the best in the world at serving it, take over immediately adjacent markets, widen the aperture of what you’re doing, and capture more and more. Once the operation is quite large, some combination of network effects, technology, scale advantages, or even brand should make it very hard for others to follow. That is the recipe for building valuable businesses.

4. Founders, and founding moments, are crucial to a company’s long-term success

The insight that foundings are crucial is what is behind the Founders Fund name. Founders and founding moments are very important in determining what comes next for a given business. If you focus on the founding and get it right, you have a chance. If you don’t, you’ll be lucky at best, and probably not even that.

The ideal is the combination of high trust people with a structure that provides a high degree of alignment. People trust each other and together create a good culture. But there’s good structure to it, too. People are rowing in the same direction, and not by accident.

5. Power law dynamics and exponential things are more common, and more powerful, than we think. For VCs to make money, a single investment must return the fund. Remember this when you’re pitching!!

If you look at Founders Fund’s 2005 fund, the best investment ended up being worth about as much as all the rest combined. And the investment in the second best company was about as valuable as number three through the rest. This same dynamic generally held true throughout the fund. This is the power law distribution in practice. To a first approximation, a VC portfolio will only make money if your best company investment ends up being worth more than your whole fund.

Despite being rooted in middle school math, exponential thinking is hard. We live in a world where we normally don’t experience anything exponentially. Our general life experience is pretty linear. We vastly underestimate exponential things. If you backtest Founders Fund’s portfolios, one heuristic that’s worked shockingly well is that you should always exercise your pro rata participation rights whenever a smart VC was leading a portfolio company’s up round. Conversely, the test showed that you should never increase your investment on a flat or down round.

6. Distribution is vastly underestimated among startup success factors. Build it and they will not come. CLV > CAC

But for whatever reason, people do not get distribution. They tend to overlook it. It is the single topic whose importance people understand least. Even if you have an incredibly fantastic product, you still have to get it out to people. The engineering bias blinds people to this simple fact. The conventional thinking is that great products sell themselves; if you have great product, it will inevitably reach consumers. But nothing is further from the truth.

It is very likely that one channel is optimal. Most businesses actually get zero distribution channels to work. Poor distribution—not product—is the number one cause of failure. If you can get even a single distribution channel to work, you have great business. If you try for several but don’t nail one, you’re finished.

Distribution isn’t just about getting your product to users. It’s also about selling your company to employees and investors. The familiar anti-distribution theory is: the product is so good it sells itself. That, again, is simply wrong.

7. What’s your secret?

What important truth do very few people agree with you on?

What great company is no one starting?

The focus should be on the secrets that matter: the big secrets that are true.

8. Are you a pessimist or optimist? Do you view the world as determinate or indeterminate? SUCH a powerful framework…

If you believe that the future is fundamentally indeterminate, you would stress diversification. This is true whether you’re optimistic or pessimistic. And indeed, chasing optionality seems to be what most everybody does. People go to junior high and then high school. They do all sorts of activities and join lots of clubs along the way. They basically spend 10 years building a diverse resume. They are preparing for a completely unknowable future. Whatever winds up happening, the diversely prepared can find something in their resume to build on.

In a strange way, China falls squarely in the determinate pessimistic quadrant. It is the opposite of the U.S.’s optimistic indeterminacy.

But the indeterminate future is somehow one in which probability and statistics are the dominant modality for making sense of the world. Bell curves and random walks define what the future is going to look like. The standard pedagogical argument is that high schools should get rid of calculus and replace it with statistics, which is really important and actually useful. There has been a powerful shift toward the idea that statistical ways of thinking are going to drive the future.

9. Great people throughout history have been both extreme insiders and extreme outsiders. Things go great (ie, you’re the King) until they don’t (ie, you get killed). Some analogues with startup founders

The dynamic might work like this. People start out being different. They are nurtured to develop their already somewhat extreme traits. Those traits become more important, and they learn to exaggerate them. Others perceive that inflated importance and exaggerate in turn. The founders thus end up being even more different than they were before. And we cycle and repeat.

And we’ll end with a powerful excerpt from Abe Lincoln:

The question then is, Can that gratification be found in supporting and maintaining an edifice that has been erected by others? Most certainly it cannot. Many great and good men, sufficiently qualified for any task they should undertake, may ever be found whose ambition would aspire to nothing beyond a seat in Congress, a gubernatorial or a presidential chair; but such belong not to the family of the lion or the tribe of the eagle. What! think you these places would satisfy an Alexander, a Caesar, or a Napoleon? Never! Towering genius disdains a beaten path. It seeks regions hitherto unexplored. It sees no distinction in adding story to story upon the monuments of fame erected to the memory of others. It denies that it is glory enough to serve under any chief. It scorns to tread in the footsteps of any predecessor, however illustrious. It thirsts and burns for distinction; and if possible, it will have it, whether at the expense of emancipating slaves or enslaving freemen. Is it unreasonable, then, to expect that some man possessed of the loftiest genius, coupled with ambition sufficient to push it to its utmost stretch, will at some time spring up among us?

Hope you enjoyed these snippets. Read the full notes on Blake’s site.